Monsaraz

Take N18 southeast (towards Beja) to the N256, which takes you through the agricultural town of Reguengos de Monsaraz to Monsaraz. Watch for the vantage point along the way where you can see the hilltop towns of Mourao and its sister, Monsaraz, to the north. It’s obvious that defense against Spanish invasion was uppermost in the mind of King Dom Diniz when he ordered these two fortified towns constructed in the 14th century. Monsaraz is steeped in authentic medieval atmosphere, but so small that it will take you only a little time (much longer if you love shopping) to explore its tiny streets and admire its views across the plain. Like Évora, Monsaraz was reclaimed from the Moors by Gerald the Fearless in the 12th century and formed an important part of the defensive scheme of subsequent Portuguese monarchs. The narrow town streets are made for wandering, and the Rua Direita, lined with ancient white houses sporting coats of arms, will transport you back in time. From the town’s 13th-century castle ramparts, it’s apparent why this spot was chosen for defense—the spectacular views stretch forever across the Alentejo Plain into Spain.